WO2007142083A1 - Material for organic electroluminescence element, and organic electroluminescence element using the material - Google Patents

Abstract

Provided are an organic electroluminescence element composed of a compound including a hetero atom having a specific structure, and an organic electroluminescence element wherein an organic thin film layer, which is composed of one or a plurality of layers including at least a light emitting layer, is sandwiched between an anode and a cathode. The organic electroluminescence element, which has high emission efficiency, no pixel defect, excellent heat resistance and a long life, is provided by permitting the organic thin film layer to include the organic EL element material. The organic electroluminescence element material for providing such organic electroluminescence element is also provided.

Description

 Specification

 ORGANIC ELECTRIC LIGHT EMITTING ELEMENT MATERIAL AND ORGANIC ELECTRIC LIGHT EMITTING ELEMENT

 Technical field

 TECHNICAL FIELD [0001] The present invention relates to a material for an organic electoluminescence device and an organic electoluminescence device using the same, and more particularly, an organic electorum having high luminous efficiency, excellent pixel resistance, excellent heat resistance, and a long lifetime. The present invention relates to a mouth luminescence element and an organic electorum luminescence element material for realizing the same.

 Background art

 [0002] Organic-electric-luminescence elements (hereinafter, electric-luminescence) may be abbreviated as EL, and the recombination energy between holes injected from the anode and electrons injected from the cathode by applying an electric field. It is a self-luminous element that utilizes the principle that fluorescent substances emit light. Eastman's Kodak's CW Tang et al. Reported low-voltage-driven organic EL devices using stacked devices (CW Tang, SA Vanslyke, Applied Physics Letters, 51 卷, 913, 1987, etc.) Since then, research on organic EL devices using organic materials as constituent materials has been actively conducted. Tang et al. Used tris (8-quinolinolato) aluminum for the light-emitting layer and a triphenylamine derivative for the hole transport layer. The advantages of the stacked structure are that it increases the efficiency of hole injection into the light-emitting layer, increases the efficiency of exciton generation by recombination by blocking electrons injected from the cathode, For example, the generated excitons are confined. As shown in this example, the organic EL device has a two-layer structure of a hole transport (injection) layer and an electron transport luminescent layer, or a hole transport (injection) layer, a luminescent layer, and an electron transport (injection) layer. The three-layer type is well known. In such a multilayer structure element, in order to increase the recombination efficiency of injected holes and electrons, the element structure and the formation method are devised.

[0003] Light-emitting materials for organic EL devices include light-emitting materials such as chelate complexes such as tris (8-quinolinolato) aluminum complex, coumarin derivatives, tetraphenylbutadiene derivatives, distyrylarylene derivatives, and oxadiazole derivatives. And they are blue It is reported that light emission in the visible region from red to red is obtained, and the realization of a color display element is expected (see, for example, Patent Document 1, Patent Document 2, Patent Document 3, etc.).

 In recent years, it has also been proposed to use a phosphorescent material in addition to a fluorescent material for the light emitting layer of an organic EL element (see, for example, Non-Patent Document 1 and Non-Patent Document 2). In this way, high emission efficiency is achieved by using the singlet state and triplet state of the excited state of the organic phosphorescent material in the light emitting layer of the organic EL element. When electrons and holes recombine in an organic EL device, it is thought that singlet excitons and triplet excitons are generated at a ratio of 1: 3 due to the difference in spin multiplicity. If a light-emitting material is used, light emission efficiency of 3 to 4 times that of an element using only fluorescence can be considered.

 [0004] In such an organic EL device, an anode, a hole transport layer, an organic light emitting layer, an electron transport layer (hole blocking) are sequentially arranged so that the triplet excited state or triplet exciton is not quenched. Layer), an electron transport layer, and a cathode are used, and a host material fluorescent compound has been used for the organic light emitting layer (for example, Patent Documents 4 to 8). Here, a host material having a dibenzofuran or dibenzothiophene skeleton is described. However, no superiority in device performance has been shown compared to other carbazolyl skeletons, and there is no description even if it is a combination with a silicon or germanium atom.

 Further, Patent Documents 9 and 10 describe a compound having a substituent such as an arylsilyl group. The compound group as in the present invention is not described, and a triplet energy gap can be kept wide. The useful effects as materials for organic EL devices, particularly blue phosphorescent devices, are also described.

 Further, Patent Documents 11 to 18 describe allylsilane and allylgerman compounds, and examples are described as host materials for blue phosphorescent elements. However, the compound group as in the present invention is described. The effect of missing is also unknown.

 Patent Document 1: Japanese Patent Laid-Open No. 8-239655

 Patent Document 2: Japanese Patent Laid-Open No. 7-138561

 Patent Document 3: JP-A-3-200889

 Patent Document 4: International Publication WO05Z101912

Patent Document 5: JP-A-5-109485 Patent Document 6: JP 2004-002351 A

 Patent Document 7: International Publication WO04Z096945

 Patent Document 8: JP 2002-308837 A

 Patent Document 9: Japanese Patent Laid-Open No. 2003-138251

 Patent Document 10: Japanese Unexamined Patent Publication No. 2000-351966

 Patent Document 11: International Publication WO04Z095598

 Patent Document 12: US 2004-209115

 Patent Document 13: Japanese Unexamined Patent Application Publication No. 2004-103463

 Patent Document 14: Japanese Unexamined Patent Application Publication No. 2005-183303

 Patent Document 15: Japanese Unexamined Patent Application Publication No. 2005-317275

 Patent Document 16: Japanese Unexamined Patent Application Publication No. 2004-200104

 Patent Document 17: Japanese Patent Application Laid-Open No. 2005-310672

 Patent Document 18: Japanese Patent Application Laid-Open No. 2005-306864

 Non-patent literature 1: D. F. O'Brien and M. A. Baldo et al. Improved energy transfenng el ectrophosphorescent devices Applied Physics letters Vol. 74 No.3, pp442 ~ 444, Jan uary 18, 1999

 Non-Patent Document 2: M. A. Baldo et al. "Very high-efficiency green organic light-emitting devices based on electrophosphorescence Applied Physics letters Vol. 75 No. 1, pp 4-6, July 5, 1999

 Disclosure of the invention

 Problems to be solved by the invention

[0006] The present invention has been made to solve the above-described problems, and has an organic EL element that has high luminous efficiency, has no pixel defects, has excellent heat resistance, and has a long lifetime, and an organic EL element that realizes the organic EL element. The purpose is to provide elemental materials.

 Means for solving the problem

[0007] As a result of intensive research to achieve the above object, the present inventors have used a compound represented by the following general formula (1) or (2) as an organic EL device material, thereby eliminating pixel defects. We found that organic EL devices with high efficiency, high heat resistance, and long life without defects were obtained. The present invention has been solved.

 That is, the present invention provides an organic EL device material having a compound power represented by the following general formula (1) or (2).

 An organic electoluminescence device material comprising a compound represented by the following general formula (1) is provided.

 [0008] [Chemical 1]

[In the general formula (1), R to R each independently represent a hydrogen atom, a halogen atom, or a substituent.

 1 8

 May have a group, may have an alkyl group having 1 to 40 carbon atoms, may have a substituent, may have a heterocyclic group having 3 to 20 carbon atoms, and may have a substituent, may have 1 to 40 carbon atoms. It may have an alkoxy group or a substituent, may have a C6-C40 non-condensed aryl group, may have a substituent, may have a C6-C12 condensed aryl group, or a substituent. Good C6-C20 aryloxy group, may have a substituent, C7-C20 aralkyl group, may have a substituent, C2-C40 alkenyl group, substituent May have 1 to 40 alkylamino groups, may have substituents 7 to 60 carbon atoms aralkylamino groups, may have substituents 3 to 20 carbon atoms alkylsilyl groups, substituted An aryl group having 8 to 40 carbon atoms which may have a group, an aralkylsilyl group having 8 to 40 carbon atoms which may have a substituent, and a carbon number having 3 to 20 carbon atoms which may have a substituent Alkyl germanium group, may have a substituent, may have 8 to 40 carbon atoms aryl germanium group, may have a substituent, 8 to 40 carbon atoms aralkyl germanium group, have substituents It may be a 7 to 40 carbon atom group which may be substituted, a halogenated alkyl group having 1 to 40 carbon atoms which may have a substituent, a cyan group or a structure represented by the following general formula (a): R ~ R

 1 8 Among them, at least one has a structure represented by the following general formula (a).

[0010] [Chemical 2] γ ₂

(In the general formula (a), L is a carbon number of 1 to 1 which may have a single bond or a substituent: an alkylene group of L0 or a carbon number which may have a substituent. 6-40 non-condensed arylene groups, with substituents

 Three

 May be a condensed arylene group having 6 to 12 carbon atoms or a substituent, and is a divalent aromatic heterocyclic group having 3 to 40 carbon atoms, and Y to Y are each independently substituted. Charcoal that may have a group

 13

 A prime alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms which may have a substituent, and an aromatic heterocyclic group having 6 to 30 carbon atoms which may have a substituent. It is an elementary atom or a germanium atom. )

 X is a sulfur atom, an oxygen atom, a substituted silicon atom represented by SIR R, or a substituted germanium atom represented by GeR R, and R 1, R 2, R and R each independently have a substituent abcd

 Or an alkyl group having 1 to 40 carbon atoms or an aryl group having 6 to 20 carbon atoms which may have a substituent. ]

[0012] [Chemical 3]

 (2)

[In the general formula (2), R 1 to R 4 and R 5 independently represent a hydrogen atom or a halogen atom.

 11 14

An alkyl group having 1 to 40 carbon atoms that may have a substituent, a heterocyclic group having 3 to 20 carbon atoms that may have a substituent, and 1 to 40 carbon atoms that may have a substituent Or a non-condensed aryl group or substituent having 6 to 40 carbon atoms, or a condensed aryl group or substituent having 6 to 12 carbon atoms. Good carbon number 6-20 aralkyl group, optionally substituted carbon number 7-20 carbon atoms, optionally substituted carbon number 2-40 alkyl groups, optionally having 1-40 alkylamino groups, optionally having substituents, 7-60 carbon atoms, having substituents Good, an alkylsilyl group having 3 to 20 carbon atoms, an arylsilylsilyl group having 8 to 40 carbon atoms which may have a substituent, a substituent group, an aralkylsilyl group having 8 to 40 carbon atoms, and a substituent. Or an alkyl germanium group having 3 to 20 carbon atoms, an aryl germanium group having 8 to 40 carbon atoms which may have a substituent, or a substituent! A 40-aralkylgermanium group, an optionally substituted ketoaryl group having 7 to 40 carbon atoms, and an optionally substituted halogenated alkyl group or cyano group having 1 to 40 carbon atoms.

 X, L and Z are the same as in general formula (1), and Y is the same as Y to Y in general formula (1). η

 13

 Is an integer from 1 to 4. ]

[0014] Further, the present invention provides an organic EL device in which an organic thin film layer comprising at least one light emitting layer or a plurality of layers is sandwiched between a cathode and an anode, wherein at least one of the organic thin film layers is the organic EL element. An organic EL device containing a device material is provided. The invention's effect

 [0015] When an organic EL device material comprising a compound represented by the general formula (1) or (2) of the present invention is used, the luminous efficiency is high, the pixel defect is excellent, the heat resistance is excellent, and the lifetime is long. Organic EL elements can be obtained.

 BEST MODE FOR CARRYING OUT THE INVENTION

[0016] The organic EL device material of the present invention also has a compound strength represented by the following general formula (1) or (2).

 First, the compound represented by the general formula (1) will be described.

 In the general formula (1), R to R

18 may each independently have a hydrogen atom, a halogen atom or a substituent, may have an alkyl group having 1 to 40 carbon atoms, may have a substituent, or a heterocyclic group having 3 to 20 carbon atoms. , An optionally substituted alkoxy group having 1 to 40 carbon atoms, may have a substituent, may have a non-condensed aryl group having 6 to 40 carbon atoms, and may have a substituent. ~ 12 condensed aryl group, optionally having 6-20 carbon atoms aryloxy group, having substituents, having 7-20 carbon atoms aralkyl group, having substituents Good, Alkenyl group having 2 to 40 carbon atoms, may have a substituent Alkylamino group having 1 to 40 carbons, may have a substituent Aralkylamino group having 7 to 60 carbon atoms, an alkylsilyl group having 3 to 20 carbon atoms that may have a substituent, an arylsilylsilyl group having 8 to 40 carbon atoms that may have a substituent, and a substituent May be an aralkylsilyl group having 8 to 40 carbon atoms, an alkylgermanium group having 3 to 20 carbon atoms which may have a substituent, an arylgermanium group having 8 to 40 carbon atoms which may have a substituent. An aralkyl germanium group having 8 to 40 carbon atoms which may have a substituent, a ketoaryl group having 7 to 40 carbon atoms which may have a substituent, and 1 to 1 carbon atoms which may have a substituent 40 halogenated alkyl groups, cyan groups, or a structure represented by the following general formula (a):

 1 8 Among them, at least one has a structure represented by the following general formula (a).

Examples of the halogen atom include fluorine, chlorine, bromine, iodine and the like. Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an s-butyl group, an isobutyl group, a t-butyl group, an n-pentyl group, an n-hexyl group, and an n-heptyl group. N-octyl group, n-nor group, n-decyl group, n-undecyl group, n-dodecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group, n- Heptadecyl group, n-octadecyl group, neopentyl group, 1-methylpentyl group, 2-methylpentyl group, 1 pentylhexyl group, 1-butylpentyl group, 1-heptyloctyl group, 3-methylpentyl group, hydroxymethyl group, 1 -Hydroxyethyl group, 2-hydroxyethyl group, 2-hydroxyisobutyl group, 1,2-dihydroxyethyl group, 1,3 dihydroxyisopropyl group, 2, 3 Dihydroxy t —butyl, 1, 2, 3 trihydroxypropyl, chloromethyl, 1-chloroethyl, 2 chloroethyl, 2 isobutyl, 1,2 dichloroethyl, 1,3 dichloro Isopropyl group, 2,3 dichloro-t-butyl group, 1,2,3 trichloropropyl group, bromomethinole group, 1-bromoethinole group, 2-bromoethinole group, 2-bromoisobutinole group, 1,2 dibromoethyl group, 1,3 dibromoisopropyl group, 2,3 dibu-ported tert-butyl group, 1,2,3 tribromopropyl group, odomethyl group, 1-dodoethyl group, 2-dosoethyl group, 2-dosobutyl group, 1,2-joule Ethyl group, 1,3 jodoisopropyl group, 2,3 jodo-t-butyl group, 1,2,3 triodopropyl group, aminomethyl group, 1 aminoethyl group, 2-aminoethyl , 2-Aminoisobuchiru group, 1, 2-di § Minoechiru group, 1, 3-di § amino isopropyl, 2, 3 Jiamino one t- butyl group, 1, 2, 3 —Triaminopropyl group, cyanomethyl group, 1-cyanoethyl group, 2-cyanoethyl group, 2cyanoisobutyl group, 1,2dicanoethyl group, 1,3dicyanoisopropyl group, 2,3dicyano-t-butyl group, 1, 2, 3 tricyanopropyl group, nitromethyl group, 1--to-ethyl group, 2-troethyl group, 1,2-dinitroethyl group, 2,3 di-t-butyl group, 1, 2, 3 tri- Examples thereof include a tropropyl group, a cyclopentyl group, a cyclohexyl group, a cyclohexyl group, and a 3,5-tetramethylcyclohexyl group.

[0018] Among these, a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an sbutyl group, an isobutyl group, a tbutyl group, an n pentyl group, an n xyl group, an n butyl group, n-octyl group, n-nor group, n-decyl group, n-undecyl group, n-dodecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group, n-pentadecyl group, n-octadecyl group, neopentyl group, 1-methylpentyl group, 1 pentylhexyl group, 1-butylpentyl group, 1 butyloctyl group, cyclohexyl group, cyclooctyl group, 3,5-tetramethylcyclohexyl group.

As the heterocyclic group, for example, 1 pyrrolyl group, 2 pyrrolyl group, 3 pyrrolyl group, pyrazinyl group, 2-pyridyl group, 1 imidazolyl group, 2-imidazolyl group, 1 pyrazolyl group, 1- Indolizyl group, 2—Indorigid group, 3—Indolizyl group, 5—Indolizyl group, 6 Indolizyl group, 7 Indolizyl group, 8 Indolizyl group, 2 Imidazopyridyl group , 3-Imidazopyridyl group, 5-Imidazopyridyl group, 6-Imidazopyridinyl group, 7-Imidazopyridyl group, 8-Imidazopyridyl group, 3-Pyridyl group, 4 Pyridyl group, 1 Indolyl Group, 2 indolyl group, 3 indolyl group, 4 indolyl group, 5—indolyl group, 6—indolyl group, 7—indolyl group, 1—isoindolyl group, 2—isoindolyl group, 3—isoindolyl group, 4 isoin Ryl group, 5—Isoindolyl group, 6—Isoindolyl group, 7 Isoindolyl group, 2 Furyl group, 3 Furyl group, 2 Benzofural group, 3—Benzofuryl group, 4 Benzofural group, 5— Benzofuller group, 6-Benzofuller group, 7 Benzofuller group, 1 Isobenzofural group, 3 Isobenzofural group, 4 Isobenzofural group, 5-Isobenzolfuran -Lole group, 6-isobenzozoll group, 7 isobenzozoll group, 2 quinolyl group, 3 quinolyl group, 4 quinolyl group, 5 quinolyl group Noryl group, 6 quinolyl group, 7 quinolyl group, 8 quinolyl group, 1 isoquinolyl group, 3 isoquinolyl group, 4 isoquinolyl group, 5-isoquinolyl group, 6-isoquinolyl group, 7-isoquinolyl group, 8 isoquinolyl group, 2 quinoxalinyl Group, 5 quinoxalinyl group, 6 quinoxalyl group, 1 primary rubazolyl group, 2—force rubazolyl group, 3—power rubazolyl group, 4 force 1 rubazolyl group, 9 force 1 rubazolyl group, j8—carboline 1yl, j8—carboline 3 yl, j8—carboline 4 yl, j8—carboline 5 yl, j8—carboline 6 yl, 13 carboline 7 ill, 13 carboline 6 ill, 13 carboline 9 yl 1 phenanthridyl group, 2 phenanthridyl group, 3 phenanthridyl group, 4 phenanthridyl group, 6 phenanthridyl group, 7 phenanthridyl group 8-phenanthryl group, 9-phenanthridyl group, 10-phenanthridyl group, 1-ataridyl group, 2-ataridyl group, 3-ataridyl group, 4-ataridyl group, 9—Atharidyl group, 1, 7 phenant port phosphorus— 2—yl group, 1, 7 phenant port ring—3—yl group, 1, 7 phenanthroline—4—yl group, 1, 7 phenant port Phosphorus—5-yl group, 1, 7 Phenant mouth phosphorus—6-—Yel group, 1, 7 Phenant mouth ring—8—Yel group, 1, 7 Phenant mouth ring—9—Yel group, 1, 7 Phenant Mouth Ring—10-yl group, 1,8 Phenant Mouth Ring—2-yl group, 1,8—Phenant Mouth Ring—3-yl group, 1,8 Phenant Mouth Ring—4-yl group, 1,8 Phenanthroline—5-yl group, 1,8 Phenant mouth ring—6-Ile group, 1,8 Phenant mouth ring—7—Yel group, 1,8 Phenant mouth ring—9—yl group 1, 8 Phenant Mouth Ring—10—yl group, 1, 9 Phenant Mouth Ring—2-yl group, 1, 9 Phenant Mouth Ring—3-yl group, 1, 9 Phenant Mouth Ring—4-yl group 1, 9 Phenant Mouth Ring—5-yl group, 1, 9 Phenanthroline—6-Mill Group, 1, 9 Phenant Mouth Ring—7—Mill Group, 1, 9 Phenant Mouth Ring—8—yl Group 1, 9 phenant ring phosphorus—10—yl group, 1,10 phenant ring phosphorus—2-—yl group, 1,10 phenant ring phosphorus—3-yl group, 1,10 phenant ring phosphorus—— 1-yl group, 2, 9-phenant mouth ring 1-yl group, 2, 9-phenant mouth ring 1-yl group, 2, 9 phenant mouth phosphorus 1 4-yl group, 2, 9 phenant ring phosphorus 5- 5-l group, 2, 9 phenant ring ring 6- yl group, 2, 9 phenant ring ring 7- yl group, 2, 9 phenant group Mouth phosphorus—8 —Yl group, 2, 9 phenantine phosphorus— 10—yl group, 2, 8 f mnan 卜 P gin 1-inole group, 2,8 f mnan 卜 P gin 3—inole group, 2, 8— 1 to 4 groups of phosphorus, 2 to 8 groups of phosphorus to 8 ports, 2 to 8 groups of 6 to 2 ports of mouth, 2 to 8 groups of 7 to 8 ports of phenol , 8 Phosphorous mouth ring 9 — yl group, 2, 8 Phosphorous mouth ring — 10 — yl group, 2, 7 Phoenant mouth ring — 1 — yl group, 2, 7 phenant mouth ring 1 — yl group , 2, 7 phenant mouth ring 4-yl group, 2, 7- phenant mouth ring 5-l group, 2, 7 phenant mouth ring 6- yl group, 2, 7 phenant mouth ring one 8- 2, 7 phenanthrine ring 9-yl group, 2, 7 phenanthrin ring 1 0-yl group, 1 phenadyl group, 2-phenadyl group, 1 phenothiazyl group, 2—Phenothiazyl group, 3 Phenothiazyl group, 4 Phenothiazyl group, 10 Phenothiazyl group, 1 Phenoxazyl group, 2 Phenoxazyl group, 3 Phenoxadi group Group, 4 phenoxazyl group, 10 phenoxazyl group, 2-oxazolyl group, 4-oxazolyl group, 5-oxazolyl group, 2 oxadiazolyl group, 5 oxadiazolyl group, 3-furazal group, 2 chalcyl group, 3-Cyl group, 2-methyl pyrrole 1-yl group, 2-methyl pyrrole 3-yl group, 2-methyl pyrrole 4-yl group, 2-methyl pyrrole 4-lu group, 3-methyl pyrrole 1-yl group 3 methyl pyrrole 2-yl group, 3 methyl pyrrole 4-yl group, 3 methyl pyrrole 5-yl group, 2-t-butyl pyrrole 4-yl group, 3- (2 phenylpropyl) pyrrole group 1-yl, 2-methyl 1 indolyl, 4-methyl-1 indolyl, 2-methyl-3 indolyl, 4-methyl-3 indolyl, 2 t-butyl 1 indolyl, 4 t butyl 1 indol Group, 2 t-butyl 3-indolyl group, 4 t-butyl 3-indolyl group, 1-dibenzofuran group, 2 dibenzofuran group, 3 dibenzofuran group, 4-dibenzofuran group, 1-dibenzothiol group 2 Dibenzothiol group, 3 Dibenzothiol group, 4-Dibenzothiol group, 1-Silafluor group, 2 Silafluor group, 3 Silafluor group, 4-Silafluor group, 1 Germafluor group- And 2 germanefluor groups, 3 germanefluore groups, 4 germanefluore groups and the like.

Among these, 2-pyridyl group, 1-indolizyl group, 2-indolidyl group, 3-indolidyl group, 5-indolidyl group, 6-indolidyl group, 7-indolidinyl group are preferable. , 8 indolizyl group, 2 imidazopyridyl group, 3 imidazopyridinyl group, 5—Imidazopyridinyl group, 6—Imidazopyridyl group, 7—Imidazopyridyl group, 8—Imidazopyridyl group, 3 Pyridyl group, 4 Pyridyl group, 1—Indolyl group, 2—India Ryl group, 3-Indolyl group, 4-Indolyl group, 5-Indolyl group, 6-Indolyl group, 7-Indolyl group, 1-Isoindolyl group, 2-Isoindolyl group, 3-Isoindolyl group, 4-Isoindolyl group, 5 —Isoindolyl group, 6-Isoindolyl group, 7—Isoindolyl group, 1—Force rubazolyl group, 2—Force rubazolyl group, 3—Force rubazolyl group, 4—Strength rubazolyl group, 9—Strength rubazolyl group, 1—Dibenzofuryl group, 2 dibenzofural group, 3 dibenzofural group, 4-dibenzofural group, 1-dibenzothiol group, 2 dibenzothiol group, 3 dibenzothiol group, 4-dibenzo group Zothiophenyl group, 1-silafluorenyl group, 2 silafluoryl group, 3 silafluoryl group, 4-silafluoryl group, 1 germanafluorenyl group, 2 germanafluorenyl group, 3 germanafluorenyl group Group, 4 is a germanafluorenyl group.

[0021] The alkoxy group is a group represented by OY, and specific examples of Y include the same as those described for the alkyl group, and preferred examples are also the same.

 Examples of the non-condensed aryl group include a phenyl group, a 2-biphenylyl group, a 3-biphenylyl group, a 4-biphenylyl group, a p-terferyl group, a 4-terphenyl group, and a p-terferyl group. Group, p terferyl 2-yl group, m-terferyl 4-yl group, m-terferol 3-yl group, m-terferyl 2-yl group, o thryl Group, m-tolyl group, ρ-tolyl group, p-t-butylphenol group, p- (2-phenylpropyl) phenol group, 4, -methylbiphenyl group, 4 "-tert-butyl-p-terphee -Lu 4-yl group, o-tame group, m-tame group, p-tame group, 2, 3 xylyl group, 3, 4 xylyl group, 2,5 xylyl group, mesityl group, m-k And water phenyl group, etc. Among these, a phenyl group, a 2-biphenyl group, a 3-biphenyl group, a 4-biphenyl group are preferable. Ruyl group, m-Terferlu group 4-yl group, m-Terferlu group 3-yl group, m-Terferlu group 2-yl group, ρ-Tolyl group, 3,4-Xylyl group, m-Quarterfe group -Lu 2—yl group.

 Examples of the condensed aryl group include a 1 naphthyl group and a 2-naphthyl group.

[0022] The allyloxy group is a group represented by OAr. The thing similar to what was demonstrated by the condensed aryl group is mentioned, A preferable example is also the same. Examples of the aralkyl group include a benzyl group, a 1-phenylethyl group, a 2-phenyl-ruethyl group, a 1-phenylisopropyl group, a 2-phenylisopropyl group, a phenyl-butinore group, and a naphthinolele. Methinole group, 1-a naphthinoreethinole group, 2-a naphthylethyl group, 1-naphthylisopropyl group, 2-a-naphthylisopropyl group, 13-naphthylmethyl group, 1-β-naphthylethyl group, 2-β-naphthylethyl group, 1 β-naphthylisopropyl group, 2-β-naphthylisopropyl group, 1 pyrrolylmethyl group, 2- (1 pyrrolyl) ethyl group, ρ-methylbenzyl group, m-methylbenzyl group, o-methenolevendinore group, p , M-black benzyleno group, o chlorobenzyl group, p bromobenzyl group, m-bromobenzyl group, o bromobenzyl group, ρ O-benzyl group, m-oodobenzyl group, o-oodobenzyl group, p-hydroxybenzyl group, m-hydroxybenzyl group, o-hydroxybenzyl group, p-aminobenzyl group, m-aminobenzyl group, o-aminobenzyl group, p-trobenzyl group, m--trobenzyl group, o-trobenzyl group, p-cyanobenzyl group, m-cyanobenzyl group, o-cyanobenzil group, 1-hydroxy-1-2-phenylisopropyl group, 1-black mouth 2 —Phenol isopyl pill group and the like.

 Among these, benzyl group, p-cyanobenzyl group, m-cyanobenzyl group, o-cyanobenzyl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group, and 2-phenylisopropyl group are preferable. It is a group.

[0023] Examples of the alkenyl group include a vinyl group, a allyl group, a 1-butenyl group, a 2-butenyl group, a 3-butyl group, a 1,3-butanegel group, a 1-methylvinyl group, a styryl group, 2, 2-diphenyl group, 1,2-diphenyl group, 1-methylaryl group, 1,1-dimethylaryl group, 2-methylaryl group, 1-alkyl-aryl group, 2-furaryl group, 3-furyl group -Luaryl group, 3,3 diphenyl-uluyl group, 1,2 dimethylaryl group, 1 ferrue 1-butur group, 3 ferulu 1-butur group, and the like are preferable, and styryl group, 2,2-diphenyl- Ruby group, 1,2-diphenyl-rubyl group and the like.

[0024] The alkylamino group, which may have a substituent, and has 7 to 60 carbon atoms. The group is represented as NQ Q. Specific examples of Q and Q are independently

1 2 1 2

 Examples are the same as those described for the alkyl group, the aryl group, and the aralkyl group, and preferred examples are also the same.

 Examples of the alkylsilyl group include a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a butyldimethylsilyl group, and a propyldimethylsilyl group.

 Examples of the arylsilyl group include a triphenylsilyl group, a tribiphenylsilyl group, a jetter ferrofurylsilyl group, a phenyldimethylsilyl group, and a t-butyldiphenylsilyl group.

 Examples of the aralkylsilyl group include a tribenzylsilyl group, a benzyldimethylsilyl group, and a t-butyldibenzylsilyl group.

[0025] Examples of the alkylgermanium group include a trimethylgermanium group, a triethylgermanium group, a t-butyldimethylgermanium group, a butyldimethylgermanium group, and a propyldimethylgermanium group.

 Examples of the aryl germanium group include a triphenylgermanium group, a triphenylgermanium group, a jetterfe roof-germanium group, a phenyldimethylgermanium group, and a t-butyldiphenylgermanium group.

 Examples of the aralkyl germanium group include a tribenzylgermanium group, a benzyldimethylgermanium group, a t-butyldibenzylgermanium group, and the like.

 The keto reel group is represented as COAr, and a specific example of Ar is the aryl group.

 twenty two

 The thing similar to what was demonstrated is mentioned, A preferable example is also the same.

 Examples of the halogenated alkyl group include those in which at least one hydrogen atom of the alkyl group is substituted with a halogen atom, and preferred examples are also the same.

In the general formula (1), X represents a sulfur atom, an oxygen atom, or a substituted silicon atom represented by SiR R a b

Or a substituted germanium atom represented by GeR R, and each of R 1, R 2, R and R is independently cdabed and has an alkyl group having 1 to 40 carbon atoms or a substituent which may have a substituent. Even so, it is an aryl group having 6 to 20 carbon atoms. Examples of the alkyl group for R, R, R, and R include the same alkyl groups as those described above for R to R. abed 1 8

 Preferred are a methyl group, an ethyl group, a propyl group and a butyl group.

 Examples of the aryl group having 6 to 20 carbon atoms of R, R, R, and R include the same as the non-condensed aryl abed 1 8 group of R to R, preferably a phenol group, p- A tolyl group and a 4-biphenyl group.

 [0027] The general formula (a) has the following structure.

 [Chemical 4]

(a)

[0028] In the general formula (a), L is a carbon atom having 1 to 1 carbon atoms which may have a single bond or a substituent: an alkylene group having L0 or a non-carbon atom having 6 to 40 carbon atoms which may have a substituent. It may have a condensed arylene group or a substituent, and may have a condensed arylene group having 6 to 12 carbon atoms or a substituent, and is a divalent aromatic heterocyclic group having 3 to 40 carbon atoms.

 As the alkylene group of L, the examples of the alkyl group described in the above R to R are divalent groups.

 1 8

 And methylene group, ethylene group, propylene group, butylene group, divalent cyclohexane group, divalent adamantane group and divalent norbornene group are preferable.

 Examples of the non-condensed arylene group of L include the examples of the non-condensed aryl group described in R to R above.

 1 8

 Divalent groups such as a phenol group, a para-bi-phenylene group, a meta-bi-phenylene group, an ortho-bi-phenylene group, an ortho-terphylene group, a meta-ter-phenylene group, and a para-terphenyl group. The group is preferred!

Examples of the condensed arylene group for L include divalent residues such as naphthalene. Examples of the aromatic heterocyclic group of L include pyridine, pyrazine, quinoline, pyrimidine, triazine, thiophene, silanole, benzofuran, benzothiophene, dibenzofuran, dibenzothiophene, carbazole, quinoline, furan, pyrrole, imidazole, pyrazole, Isothia Sol, isoxazole, isoquinoline, quinazoline, quinolidine, quinoxaline, cinnoline

, Benzimidazole, imidazopyridine, naphthyridine, 1,2-benzisoxazole, benzoxazonole, benzothiazonole, oxazolopyridine, isothiazolopyridine, divalent with benzocenyl skeleton Residues are mentioned, and divalent groups having a skeleton of pyridine, pyrazine, quinoline, pyrimidine, thiophene, silanole, dibenzofuran, dibenzothiophene, imidazopyridine, benzimidazole skeleton are preferred.

[0029] In the general formula (a), Y to Y each independently has 1 carbon atom which may have a substituent.

 13

 An alkyl group having ˜10, an aryl group having 6 to 20 carbon atoms which may have a substituent, and an aromatic heterocyclic group having 6 to 30 carbon atoms which may have a substituent.

 Examples of the alkyl group of Υ to Υ include the same examples as R to R above.

 1 3 1 8

 Examples of Y to Y aryl groups include R to R non-condensed aryl groups and condensed aryl groups.

1 3 1 8

 Examples similar to the groups are given.

 Examples of the aromatic heterocyclic group of Y to Y include a furyl group, a chael group, a pyrrolyl group,

13

 Midazolyl, pyrazolyl, isothiazolyl, isoxazolyl, pyridyl, pyrimidyl, quinolyl, isoquinolyl, quinazolinyl, quinolidinyl, quinoxalinyl, cinnoyl, benzimidazolyl, imidazopyridyl, benzofuryl Group, naphthyridyl group, 1,2-benzoisoxazolyl group, benzoxazolyl group, benzothiazolyl group, oxazolopyridyl group, isothiazolopyridyl group, benzocenyl group, etc. .

 In the general formula (a), Z is a silicon atom or a germanium atom.

Next, the compound represented by the general formula (2) will be described.

 [Chemical 5]

In the general formula (2), R 1 to R 4 and R 5 are each independently a hydrogen atom or a halogen atom. An alkyl group having 1 to 40 carbon atoms that may have a substituent, a heterocyclic group having 3 to 20 carbon atoms that may have a substituent, and 1 to 40 carbon atoms that may have a substituent Or a non-condensed aryl group or substituent having 6 to 40 carbon atoms, or a condensed aryl group or substituent having 6 to 12 carbon atoms. Good aralkyl group having 6 to 20 carbon atoms, aralkyl group having 7 to 20 carbon atoms that may have a substituent, alkenyl group having 2 to 40 carbon atoms that may have a substituent, and substituent May have 1 to 40 alkylamino groups and substituents, may have 7 to 60 carbon atoms aralkylamino groups and may have substituents, and may have 3 to 20 carbon atoms alkylsilyl groups and substituents May have an aryl group having 8 to 40 carbon atoms and a substituent, may have an aralkylsilyl group having 8 to 40 carbon atoms, and may have a substituent. Alkyl germanium group having 3 to 20 carbon atoms, aryl germanium group having 8 to 40 carbon atoms which may have a substituent, may have a substituent !, aralkyl germanium group having 8 to 40 carbon atoms, substituted A C 7-40 ketoaryl group which may have a group, a C 1-40 halogenated alkyl group or a cyano group which may have a substituent.

 Specific examples of these groups include the same examples as those described for R to R in the general formula (1).

 1 8

I can get lost.

 In the general formula (2), X, L and Z are the same as those in the general formula (1), Y is the same as Y to Y in the general formula (1), and specific examples and preferred examples are also the same. .

 13

 In the general formula (2), η is an integer of 1 to 4, and an appropriate molecular weight of 2 to 3 is preferable because it sufficiently satisfies both sublimation and thermal stability.

 The compound represented by the general formula (2) is preferably a compound represented by the following general formula (3) or (4) because the production becomes easy.

[Chemical 6]

In the general formulas (3) and (4), R to R are the same as R to R and R in the general formula (2),

 11 17 11 14

The same applies to specific examples and preferred examples. The same applies to L, X, Z, Y and n.

Examples of the substituent for each group represented by the general formulas (1) to (4) include an alkyl group (methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group). Group, n pentyl group, n-hexyl group, n-heptyl group, n-octyl group, hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 2-hydroxyisobutyl group, 1, 2 dihydroxyethyl group, 1,3 dihydroxyisopropyl group, 2,3-dihydroxyt-butyl group, 1,2,3 trihydroxypropyl group, chloromethyl group, 1-chloroethyl group, 2-chloroethyl group 2-chloro-isobutyl group, 1,2-dichloroethyl group, 1,3-dichloroisopropinole group, 2,3-dichloro-t-butynole group, 1,2,3 tri-chloropropyl group, bromomethyl group, 1 bromoethyl group, 2— Lomoethyl group, 2-bromoisobutyl group, 1,2 dibromoethyl group, 1,3 dibromoisopropyl group, 2,3 dibromo-t-butyl group, 1,2,3 tribromopropyl group, odomethyl group, 1-odoethyl group, 2 — Odoethyl group, 2 — odoisobutyl group, 1, 2 — jodoethyl group, 1, 3 jodoisopropyl group, 2, 3 jodo — t-butyl group, 1, 2, 3 triodopropyl group, aminomethyl group, 1-amino Ethyl group, 2-aminoethyl group, 2-aminoisobutyl group, 1,2 diaminoethyl group, 1,3 diaminoisopropyl group, 2,3 diamino-tert-butyl group, 1,2,3 triaminopropyl Group, cyanomethyl group, 1-cyanoethyl group, 2cyanoethyl group, 2cyanoisobutyl group, 1,2dicanoethyl group, 1,3dicyanopropyl group, 2,3dicyano-t-butyl group 1, 2, 3 tricyanopropyl group, nitromethyl group, 1-troethyl group, 2--troethyl group, 2--troisobutyl group, 1,2-di-troethyl group, 1,3 di-troisopropyl group, 2, 3 di-tallow t-butyl group, 1, 2, 3 tri-tropropyl group, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, 4-methylcyclohexyl group, 1-adamantyl group, 2 adamantyl group Group, 1 norbol group, 2 norbol group, etc.), C 1-6 alkoxy group (ethoxy group, methoxy group, i propoxy group, n propoxy group, s butoxy group, t butoxy group, pentoxy group) Hexinorexi group, cyclopentoxy group, cyclohexenoreoxy group, etc.), aryl group having 5 to 40 nucleus atoms, aryl group having 5 to 40 nucleus atoms substituted Examples thereof include an mino group, an ester group having an aryl group having 5 to 40 nuclear atoms, an ester group having an alkyl group having 1 to 6 carbon atoms, a cyan group, a nitro group, and a halogen atom.

 Specific examples of the organic EL device material comprising the compound represented by any one of the general formulas (1) to (4) of the present invention are shown below. The power is not limited to these exemplified compounds.

[Chemical 7]

[8 ^] [SSOO]

le ^] [9εοο]

[0037] [Chemical 10]

[0038] [Chemical 11]

[0039] The organic EL device material of the present invention is a host material contained in the light emitting layer of the organic EL device. I like it.

 Next, the organic EL device of the present invention will be described.

 The organic EL device of the present invention is an organic EL device in which at least one organic thin film layer having at least a light emitting layer or a plurality of organic thin film layers is sandwiched between a cathode and an anode. Contains materials for organic EL devices.

 As the structure of the multilayer organic EL device, for example, anode / hole transport layer (hole injection layer) Z light emitting layer Z cathode, anode Z light emitting layer Z electron transport layer (electron injection layer) Z cathode, anode Z positive Hole Transport Layer (Hole Injection Layer) Z Light Emission Layer Z Electron Transport Layer (Electron Injection Layer) Z Cathode, Anode Z Hole Transport Layer (Hole Injection Layer) Z Light Emission Layer Z Hole Barrier Layer Z Electron Transport Layer ( Electron injection layer) A layer laminated with a multilayer structure such as a Z cathode.

 [0040] In the organic EL device of the present invention, the light emitting layer preferably contains the organic EL device material of the present invention as a host material. Further, the light emitting layer is preferably a phosphorescent light emitting material and a host material, and the host material is preferably the organic EL element material.

 Phosphorescent light-emitting materials include compounds containing iridium), osmium (Os), or platinum (Pt) metals in that the external quantum efficiency of light-emitting devices with high phosphorescence quantum yields can be improved. Among the metal complexes such as iridium complexes, osmium complexes, and platinum complexes that are preferable, ortho-metalated iridium complexes are more preferable, with iridium complexes and platinum complexes being more preferable. More preferable forms of the ortho-metal 匕 metal complex include the following iridium complexes.

[0041] [Chemical 12]

[0042] [Chemical 13] (K-10) (K-11) (K-12)

 (K-13) ") (Κ-15)

In the organic EL device of the present invention, the light emitting layer preferably contains a host material and a phosphorescent light emitting material, and the phosphorescent light emitting material is preferably a light emitting material having a metal carbene carbon bond.

 Further, as the blue metal complex, which preferably contains the blue metal complex whose wavelength of maximum emission luminance is 500 nm or less, examples of the blue metal complex include the above-described K—, K 2, K 3 , K10, K11, K12, K15, K16 and K17.

The organic EL device of the present invention has a hole transport layer (hole injection layer) and the hole transport layer (hole The organic EL element of the present invention, which is preferable even if the injection layer) contains the material for the organic EL device of the present invention, has an electron transport layer (electron injection layer) and / or a hole barrier layer, and the electron transport It is preferable that the layer (electron injection layer) and the Z or hole blocking layer contain the organic EL device material of the present invention.

 [0044] The hole injection layer is a layer provided in order to efficiently inject holes into the organic EL element in addition to the anode cap. The anode force smoothly injects holes into the layer, so that the driving voltage is increased. Can be lowered, and changes in carrier balance due to driving can be suppressed. As a material used for the hole injection layer, a compound having an ionic potential energy close to the work function of the anode metal is generally used. For example, various metal complexes such as arylamine compounds, copper and iridium, hexazatrephelene derivatives and the like can be mentioned.

[0045] The hole transport layer is a layer having a function of transporting holes injected from the anode and reaching the light emitting layer. By providing the hole transport layer, holes and electrons are efficiently recombined in the light emitting layer, and the light emission efficiency can be increased. For this reason, the material used for the hole transport layer is required to have a function of efficiently transmitting holes to the light emitting layer. In general, arylene-based materials are used as materials for the hole transport layer. A material generally SeianaUtsuri Dodo is obtained first power of the value of 2 minutes with a 10- ⁵ cm ² / Vs or more in the range of 300~800 (V / cm) ^1/2 of the electric field strength is preferredゝ. It is preferable that the hole injection layer contains the organic EL device material of the present invention in the hole transport layer.

 [0046] The hole blocking layer is a layer provided between the light emitting layer and the negative electrode in order to efficiently recombine electrons and holes in the light emitting layer. For the hole blocking layer, a substance having a first oxidation potential higher than that of the light emitting layer material is used, thereby preventing injection of holes into the electron transporting layer. Examples of the material used for the hole blocking layer include a hole blocking layer material described in Japanese Patent No. 2673261.

[0047] The electron transport layer is a layer having a function of transporting electrons injected from the cathode and reaching the light emitting layer. By providing the electron transport layer, holes and electrons can be efficiently recombined in the light emitting layer, and the light emission efficiency can be increased. In order to emit EL efficiently, it is necessary to efficiently transmit electrons to the light emitting layer. Materials used for the electron transport layer include nitrogen-containing materials. In general, aromatic compound materials, hetero compounds other than nitrogen such as silole compounds, metal complexes such as aluminum and gallium, condensed aromatic hydrocarbons and the like are used. Electron mobility of this good Una material is typically 1 square of the value of the half of the electric field strength is 300 to 800 (VZC m) at ^half the range 10- ⁶ cm ² ZVS more. As the electron transporting material, materials described later are preferable. It is also preferred that the electron transport layer contains the organic EL device material of the present invention in the hole barrier layer.

 [0048] The electron injection layer is a layer provided for efficiently injecting electrons into the cathode-power organic EL device. By providing the electron injecting layer, electrons can be smoothly injected even with the cathode force, so that the driving voltage can be lowered and the change in carrier balance due to driving can be suppressed. As a material constituting the electron injection layer, materials described later are preferably exemplified.

 [0049] The organic EL device of the present invention is preferably formed by adding a reducing dopant to the interface region between the cathode and the organic thin film layer.

 Examples of the reducing dopant include alkali metals, alkali metal complexes, alkali metal compounds, alkaline earth metals, alkaline earth metal complexes, alkaline earth metal compounds, rare earth metals, rare earth metal complexes, and rare earth metal compounds. At least one kind selected.

 [0050] Examples of the alkali metal include Na (work function: 2.36 eV), K (work function: 2.28 eV), R b (work function: 2.16 eV), Cs (work function: 1.95 eV), and the like. Particularly preferred are those having a work function of 2.9 eV or less. Of these, K, Rb and Cs are preferred, Rb or Cs is more preferred, and Cs is most preferred.

 Examples of the alkaline earth metal include Ca (work function: 2.9 eV), Sr (work function: 2.0 to 2.5 eV), Ba (work function: 2.52 eV), and the like. Particularly preferred is 9 eV or less.

 Examples of the rare earth metal include Sc, Y, Ce, Tb, and Yb, and those having a work function of 2.9 eV or less are particularly preferable.

Among the above metals, preferred metals are capable of improving the light emission luminance and extending the life of organic EL devices by adding a relatively small amount to the electron injection region, which has a particularly high reducing ability. [0051] Examples of the alkali metal compound include Li 0, Cs 0, KO and other alkali oxides, LiF, N

 2 2 2

 Examples include alkali halides such as aF, CsF, KF, etc., and alkalis such as LiF, Li 0, NaF

 2

 Preference is given to oxides or alkali fluorides.

 Examples of the alkaline earth metal compound include BaO, SrO, CaO, and Ba Sr し た (0 <χ <1) mixed with these, Ba Ca O (0 <x <1), BaO, SrO, CaO is preferred x l-χ x 1-χ

 Good.

 Examples of the rare earth metal compound include YbF, ScF, ScO, YO, CeO, GdF, and TbF.

 3 3 3 2 3 2 3 3 and the like, and YbF, ScF, and TbF are preferable.

 3 3 3 3

 [0052] The alkali metal complex, alkaline earth metal complex, and rare earth metal complex are particularly those containing at least one of an alkali metal ion, an alkaline earth metal ion, and a rare earth metal ion, respectively, as the metal ion. There is no limitation. The ligands include quinolinol, benzoquinolinol, ataridinol, phenanthridinol, hydroxyphenylazole, hydroxyphenylthiazole, hydroxydiaryloxadiazole, hydroxydiarylthiadiazole, hydroxy Phenylvinylidine, hydroxyphenylbenzimidazole, hydroxybenzotriazole, hydroxyfulborane, bipyridyl, phenanthrin, phthalocyanine, porphyrin, cyclopentagen, 13-diketones, azomethines, and their derivatives Is preferable, but is not limited thereto.

[0053] As a form of addition of the reducing dopant, it is preferable to form a layered or island-like shape in the interface region. As a forming method, a reducing dopant is deposited by resistance heating vapor deposition, and a light emitting material that forms an interface region and an organic substance that is an electron injection material are simultaneously deposited, and the reducing dopant is dispersed in the organic substance. Favored ,. The dispersion concentration is organic matter: reducing dopant = 100: 1 to 1: 100, preferably 5: 1 to L: 5 in molar ratio.

 When forming the reducing dopant in layers, after forming the light emitting material or electron injecting material that is the organic layer at the interface into layers, the reducing dopant is vapor-deposited by resistance heating vapor deposition alone, preferably the layer thickness 0 Form with l-15nm.

When the reducing dopant is formed in an island shape, the light-emitting material or electron that is the organic layer at the interface After the injection material is formed into an island shape, the reducing dopant is independently deposited by resistance heating vapor deposition, preferably with an island thickness of 0.05 to lnm.

 Moreover, as a ratio of the main component and the reducing dopant in the organic EL device of the present invention, the main component: the reducing dopant is preferably 5: 1 to 1: 5 in a molar ratio, and 2: 1 to 1: 2. Is more preferable.

 [0054] The organic EL device of the present invention has an electron injection layer between the light emitting layer and the cathode, and improves adhesion to the cathode when the electron injection layer contains a nitrogen-containing ring derivative as a main component. This is preferred because of the increased molecular skeleton.

 As the electron transport material used for the electron injection layer, an aromatic heterocyclic compound containing at least one hetero atom in the molecule is preferably used, and a nitrogen-containing ring derivative is particularly preferable.

 [0055] As the nitrogen-containing ring derivative, for example, a compound represented by the general formula (A) is preferable.

 [Chemical 14]

[0056] R ^{2 to} R ⁷ are each independently a hydrogen atom, a halogen atom, an oxy group, an amino group, or a hydrocarbon group having 1 to 40 carbon atoms, and these have a substituent. Yo ...

 Examples of the halogen atom include the same ones as described above. Examples of the amino group having a substituent include the same groups as the alkylamino group, arylamino group, and aralkylamino group.

Examples of the hydrocarbon group having 1 to 40 carbon atoms include a substituted or unsubstituted alkyl group, alkenyl group, cycloalkyl group, alkoxy group, aryl group, heterocyclic group, aralkyl group, aryloxy group, alkoxycarbo group. And the like. This alkyl group, Examples of the alkyl group, cycloalkyl group, alkoxy group, aryl group, heterocyclic group, aralkyl group, and aryloxy group are the same as those described above, and the alkoxy carbo group is represented as —COOY ′. , Y ′ includes the same alkyl groups as those described above.

 M is aluminum (A1), gallium (Ga) or indium (In), and is preferably In.

 L in the general formula (A) is a group represented by the following general formula (Α ') or (Α ").

 [Chemical 15]

(Wherein R ^{8 to} R ¹² are each independently a hydrogen atom or a substituted or unsubstituted hydrocarbon group having 1 to 40 carbon atoms, and groups adjacent to each other may form a cyclic structure. R ^{13 to} R ²⁷ are each independently a hydrogen atom or a substituted or unsubstituted hydrocarbon group having 1 to 40 carbon atoms, and groups adjacent to each other may form a cyclic structure. )

[0058] The general formula (A,) and a hydrocarbon group of R ⁸ to R ¹² and R ¹³ to R ²⁷ are carbon atoms show 1 to 40 (A "), and specific examples of the R ² to R ⁷ The same thing is mentioned.

In addition, when the adjacent groups of R ^{8 to} R ¹² and R ^{13 to} R ²⁷ form a cyclic structure, examples of the divalent group include a tetramethylene group, a pentamethylene group, a hexamethylene group, diphenylmethane— 2, 2,-diyl group, diphenylane-3, 3,-diyl group, diphenylpropan 4, 4 'diyl group and the like.

[0059] Specific examples of the nitrogen-containing ring metal chelate complex represented by the general formula (A) are shown below.

[0060] [Chemical 17] //: / O Ϊί6090 / -00ί1 £ ε80ΖΗ / -00ίAV εε

ssoo

As the nitrogen-containing ring derivative, a nitrogen-containing 5-membered ring derivative is also preferable. As the nitrogen-containing 5-membered ring, an imidazole ring, a triazole ring, a tetrazole ring, an oxadiazole ring, a thiadiazole oxatriazole ring, a thiatriazole ring A nitrogen-containing 5-membered ring The derivatives include a benzimidazole ring, a benzotriazole ring, a pyridinoimidazole ring, a pyrimidinoimidazole ring, and a pyridazinoimidazole ring, and particularly preferably those represented by the following general formula (B).

 [0063] [Chemical 19]

[0064] In the general formula (B), L ^D represents a divalent or higher valent linking group, for example, carbon, silicon, nitrogen, boron, oxygen, sulfur, metal (for example, barium, beryllium), aromatic carbonization. Examples thereof include a hydrogen ring and an aromatic complex ring. Among these, a carbon atom, a nitrogen atom, a carbon atom, a boron atom, an oxygen atom, a sulfur atom, an aryl group, and an aromatic heterocyclic group are preferred. Further, a silicon atom, an aryl group, and an aromatic heterocyclic group are more preferable.

L ^B of Ariru group and an aromatic heterocyclic group good Mashiku alkyl group as Yogu substituent may have a substituent, Aruke - group, an alkyl group, Ariru group, an amino group, an alkoxy group , Aryloxy group, acyl group, alkoxycarbonyl group, aryloxycarbol group, acyloxy group, acylamino group, alkoxycarbolamamino group, aryloxycarbolamino group, sulfo-lumino group, sulfamoyl group, strong rubamoyl Group, alkylthio group, arylthio group, sulfol group, halogen atom, cyano group and aromatic heterocyclic group, more preferably alkyl group, aryl group, alkoxy group, aryloxy group, halogen atom, cyano group and aromatic group. A heterocyclic group, more preferably an alkyl group, an aryl group, an alkoxy group, an aryloxy group, an aromatic group. A heterocyclic group, particularly preferably § alkyl group, Ariru group, an alkoxy group, an aromatic heterocyclic group.

[0065] Specific examples of L ^B are listed below.

[Chemical 20] — C— One Si— -Ge— N

.B.

X ^B2 in the general formula (B) represents O—S— or = N—R ^B2 . R ^B2 represents a hydrogen atom, an aliphatic hydrocarbon group, an aryl group or a heterocyclic group.

The aliphatic hydrocarbon group for R ^B2 is a linear, branched or cyclic alkyl group (preferably an alkyl group having 120 carbon atoms, more preferably 112 carbon atoms, and particularly preferably 18 carbon atoms, , Methyl, ethyl, isopropyl, t-butyl, n-octyl, n-decyl, nxadecyl, cyclopropyl, cyclopentyl, cyclohexyl, etc.), an alkenyl group (preferably having 220 carbon atoms, more preferably Has 2 12 carbon atoms, particularly preferred Is an alkenyl group having 2 to 8 carbon atoms, and examples thereof include bur, allyl, 2 butyr, and 3 pentenyl. ), An alkyl group (preferably an alkyl group having 2 to 20 carbon atoms, more preferably 2 to 12 carbon atoms, particularly preferably 2 to 8 carbon atoms, such as propargyl and 3-pentyl. Etc.) and is preferably an alkyl group.

[0067] The aryl group of R ^B2 is a single ring or a condensed ring, preferably an aryl group having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and further preferably 6 to 12 carbon atoms. , Phenyl, 2-methylphenol, 3-methylphenyl, 4-methylphenol, 2-methoxyphenyl, 3-trifluoromethyl, pentafluorophenyl, 1-naphthyl, 2-naphthyl, etc. Is mentioned.

[0068] The heterocyclic group of R ^B2 is a monocyclic ring or a condensed ring, preferably a heterocyclic group having 1 to 20 carbon atoms, more preferably 1 to 12 carbon atoms, and further preferably 2 to 10 carbon atoms. An aromatic heterocyclic group containing at least one of a nitrogen atom, an oxygen atom, a sulfur atom and a selenium atom is preferred. Examples of this heterocyclic group include, for example, pyrrolidine, piperidine, piperazine, morpholine, thiophene, selenophene, furan, pyrrole, imidazole, pyrazole, pyridine, pyrazine, pyridazine, pyrimidine, triazole, triazine, indole. , Indazole, purine, thiazoline, thiazole, thiadiazole, oxazoline, oxazole, oxazolazole, quinoline, isoquinoline, phthalazine, naphthyridine, quinoxaline, quinazoline, cinnoline, pteridine, atridine, phenanthorin, phenazine, tetrazole, benzimidazole, benzoimidazole Oxazonole, benzothiazonole, benzotriazolene, tetrazaindene, carbazole, azepine, etc., preferably, furan, Phen, pyridine, pyrazine, pyrimidine, pyridazine, triazine, quinoline, phthalazine, naphthyridine, quinoxaline, and quinazoline are more preferable, and furan, thiophene, pyridine, and quinoline are more preferable, and quinoline is more preferable.

[0069] substituent group aliphatic hydrocarbon group represented by R ^B2, Ariru group and heterocyclic group have substituents! /, As Yogu substituent also is represented by L ^B Are the same as those mentioned above, and preferred substituents are also the same.

R ^B2 is preferably an aliphatic hydrocarbon group, an aryl group or a heterocyclic group, more preferably an aliphatic hydrocarbon group (preferably having a carbon number of 6 to 30, more preferably a carbon number of 6 to 20, Preferably an aryl hydrocarbon group, more preferably an aliphatic hydrocarbon group (preferably having a carbon number of 1-20, more preferably having a carbon number of 1-12, and further preferably having a carbon number of 2). ~ 10 things).

X ⁸² is preferably —O—, = N—R ^B2 , more preferably = N—R ^B2 , and particularly preferably = N—R ^B2 .

[0070] Z ^B2 represents an atomic group necessary for forming an aromatic ring. Specific examples of the aromatic ring formed by Z ^B2 may be either an aromatic hydrocarbon ring or an aromatic heterocyclic ring include, for example, a benzene ring, a pyridine ring, a pyrazine ring, a pyrimidine ring, a pyridazine ring, a triazine ring, Examples include pyrrole ring, furan ring, thiophene ring, selenophene ring, terorophene ring, imidazole ring, thiazole ring, selenazole ring, tellurazole ring, thiadiazole ring, oxadiazole ring, and pyrazole ring, preferably benzene. Ring, pyridine ring, pyrazine ring, pyrimidine ring and pyridazine ring, more preferably benzene ring, pyridine ring and pyrazine ring, further preferably benzene ring and pyridine ring, particularly preferably pyridine ring.

[0071] The aromatic ring formed by Z ^B2 may further have a substituent which may form a condensed ring with another ring. The substituent is exemplified ones the same way as a substituent group represented by L ^B, preferably an alkyl group, Aruke - group, an alkyl group, Ariru group, an amino group, an alkoxy group, Ariruokishi Group, acyl group, alkoxycarbonyl group, aryloxycarbonyl group, acyloxy group, acylamino group, alkoxycarbolamamino group, aryloxycarbolamamino group, sulfo-lumino group, sulfamoyl group, carbamoyl group Alkylthio group, arylthio group, sulfol group, halogen atom, cyano group, and heterocyclic group, more preferably alkyl group, aryl group, alkoxy group, aryloxy group, halogen atom, cyano group, and heterocyclic group. More preferably an alkyl group, an aryl group, an alkoxy group, an aryloxy group, or an aromatic heterocyclic group. Ri, particularly preferably Al kill group, Ariru group, an alkoxy group, an aromatic heterocyclic group.

n ^B2 is an integer of 1 to 4, preferably 2 to 3.

[0072] Among the nitrogen-containing five-membered ring derivatives represented by the general formula (B), those represented by the following general formula (Β ') are more preferable! /. [Chemical 21]

In the general formula (Β ′), R ^B71 R ^B72 and R ^B73 are the same as R ^B2 in the general formula (B), respectively, and the preferred ranges are also the same.

Z ^B71 Z ^B72 and Zeta ^Beta73 are similar to Zeta ^B2 in the general formula (beta) respectively, and the preferred ranges are also the same.

L ^B71 L ^B72 and L ^B73 each represent a linking group, the general formula (B) example divalent and was intended and single bond L ^B can be mentioned in, preferably, a single bond, a divalent aromatic hydrocarbon A hydrogen ring group, a divalent aromatic heterocyclic group, and a linking group having a combination force thereof, more preferably a single bond. L ^B71 L ^B72 and L ^B73 are the same as those exemplified as the substituents of the group as the Yogu substituent group which may have a substituent represented by L ^B in the foregoing formula (B), it was or The same is true for the preferred! / ヽ substituents.

 Y represents a nitrogen atom, a 1, 3, 5-benzenetriyl group or a 2, 4, 6-triazine triyl group. The 1, 3, 5-benzenetriyl group may have a substituent at the 2, 4, 6-position. Examples of the substituent include an alkyl group, an aromatic hydrocarbon ring group, and a halogen atom. Are listed.

 Specific examples of the nitrogen-containing 5-membered ring derivative represented by the general formula (B) or (Β ′) are shown below, but are not limited to these exemplified compounds.

[Chemical 22] / v: / O s6090 / -00ifcl £ ε80ΖΗ / -00ίAV 0

^ §≥0s

As the compound constituting the electron injection layer and the electron transport layer, in addition to the material for the organic EL device of the present invention, an electron-deficient nitrogen-containing 5-membered ring or an electron-deficient nitrogen-containing 6-membered ring skeleton, Also includes compounds having a structure combining an unsubstituted indole skeleton, a substituted or unsubstituted force rubazole skeleton, a substituted or unsubstituted aza force rubazole skeleton, and the like. Suitable electron-deficient nitrogen-containing 5-membered rings or electron-deficient nitrogen-containing 6-membered ring skeletons include pyridine, pyrimidine, pyrazine, triazine, triazole, oxadiazole, pyrazole, imidazole, quinoxaline, pyrrole skeleton and the like. And molecular skeletons such as benzimidazole and imidazopyridine which are condensed with each other. Among these combinations, a pyridine, pyrimidine, pyrazine, and triazine skeleton, and a carbazole, indole, azacarbazole, and quinoxaline skeleton are preferable. The aforementioned skeleton can be substituted and can be either V ヽ or unsubstituted! /.

 Specific examples of the electron transporting compound are shown below.

[0077] [Chemical 24]

[0078] [Chemical 25]

[0079] The electron injecting layer and the electron transporting layer may have a single-layer structure composed of one or more of the materials described above, and may have a multi-layer structure having a multi-layer force of the same or different composition. Yo ... These are preferably π-electron deficient nitrogen-containing heterocyclic groups.

 [0080] In addition to the nitrogen-containing ring derivative, it is preferable to use an insulator or a semiconductor as an inorganic compound as a constituent of the electron injection layer. If the electron injection layer is made of an insulator or a semiconductor, current leakage can be effectively prevented and the electron injection property can be improved.

Such insulators include alkali metal chalcogenides, alkaline earth metal chalcogenides, alkali metal halides and alkaline earth metal halide power groups. It is preferred to use at least one metal compound selected from If the electron injection layer is composed of such an alkali metal chalcogenide or the like, it is preferable in that the electron injection property can be further improved. Specifically, preferred alkali metal chalcogenides include, for example, Li 0, K 0, Na S, Na Se and Na 2 O, and preferred alkaline earths

 2 2 2 2 2

 Examples of the metal chalcogenide include CaO, BaO, SrO, BeO, BaS, and CaSe. Preferred alkali metal halides include, for example, LiF, NaF, KF, LiCl, KC1, and NaCl. Further, preferable alkaline earth metal halides include fluorides such as CaF, BaF, SrF, MgF, and BeF, and fluorine.

 2 2 2 2 2

 Halides other than nitrides may be mentioned.

 Semiconductors include Ba, Ca, Sr, Yb, Al, Ga, In, Li, Na, Cd, Mg, Si, Ta,

One kind or a combination of two or more kinds of oxides, nitrides or oxynitrides containing at least one element of Sb and Zn can be used. Further, the inorganic compound constituting the electron injection layer is preferably a microcrystalline or amorphous insulating thin film. If the electron injection layer is composed of these insulating thin films, a more uniform thin film can be formed, and pixel defects such as dark spots can be reduced. In addition, as such an inorganic compound,

And alkali metal chalcogenides, alkaline earth metal chalcogenides, alkali metal halides, and alkaline earth metal halides.

 In addition, the electron injection layer in the present invention preferably contains the aforementioned reducing dopant.

 In the present invention, the anode of the organic EL element plays a role of injecting holes into the hole transport layer or the light emitting layer, and it is effective to have a work function of 4.5 eV or more. . Specific examples of the anode material used in the present invention include indium tin oxide alloy (ITO), acid tin (NESA), gold, silver, platinum, copper, and the like. The cathode is preferably made of a material having a low work function for the purpose of injecting electrons into the electron injection layer or the light emitting layer. The cathode material is not particularly limited, and specifically, indium, aluminum, magnesium, magnesium indium alloy, magnesium aluminum alloy, aluminum lithium alloy, aluminum-scandium-lithium alloy, magnesium-silver alloy and the like can be used.

[0082] The method for forming each layer of the organic EL device of the present invention is not particularly limited. Conventional vacuum A forming method such as an evaporation method or a spin coating method can be used. The organic thin film layer containing the compound represented by the general formula (1) or (2) used in the organic EL device of the present invention is dissolved in a vacuum deposition method, a molecular beam deposition method (MBE method) or a solvent. The solution can be formed by a known method using a coating method such as a dipping method, a spin coating method, a casting method, a bar coating method, or a roll coating method.

 The film thickness of each organic layer of the organic EL device of the present invention is not particularly limited, but in general, if the film thickness is too thin, defects such as pinholes are generated. Usually, the range of several nm to 1 μm is preferable because of worsening.

 Example

 [0083] Next, the present invention will be described in more detail using examples.

 Synthesis Example 1: Synthesis of Compound A-2

 Compound A-2 was synthesized by the following synthesis route.

 [Chemical 26]

 Intermediate A

[0084] 4-dibenzofuranboronic acid 3.12 g, 1-bromo-3-iodobenzene 4.07 g, tetrakistriphenylphosphine palladium (0) 0.33 g, 2M aqueous sodium carbonate solution 25 g, dimethoxyethane 70 ml were placed in a flask. The mixture was heated to reflux for 8 hours under an argon atmosphere. After confirming the completion of the reaction by thin layer chromatography (TLC), add dichloromethane, wash with water and saturated brine, separate the organic layer, dry the organic layer with magnesium sulfate, filter and concentrate, yellow oil A material was obtained. After purification by column chromatography, 4.13 g of a white solid (89% yield, intermediate A) was obtained. The results of FD-MS (field desorption mass analysis) measurements are shown below.

FD— MS: calcd CH BrO 323.18, found 323 Next, put the entire amount of Intermediate A into a flask, add 4 Oml of dehydrated ethyl ether and 30 ml of dehydrated tetrahydrofuran under an argon atmosphere, dissolve with stirring, and cool to 60 ° C in a MeOH-dry ice bath. H 1. 10 ml of 6M normal butyl lithium hexane solution was added dropwise with a syringe. After stirring for 15 minutes, a solution prepared by dissolving 1.35 ml of dichlorodiphenylsilane in 10 ml of dehydrated tetrahydrofuran was added dropwise. After the temperature was raised to 5 ° C, the completion of the reaction was confirmed by TLC, and the reaction was completed by adding a saturated aqueous solution of ammonium chloride. Dichloromethane was added, washed with water and saturated brine, the organic layer was separated, the solution was dried over magnesium sulfate, filtered and concentrated to give a colorless oil. After purification by column chromatography, a white solid was obtained. This was washed again with hexane and dried to obtain 2.42 g of Compound A-2 (yield 56%). The results of FD-MS measurements on this product are shown below.

FD-MS: calcd C H 0 Si 668.85, found 668

 48 32 2

The resulting I匕合product A- 2 was used in the deposition 320 ° C, purified by sublimation at 1. ³ X 10- 3 Torr. High-performance liquid chromatography (HPLC) purity was 99.5%.

Synthesis Example 2: Synthesis of Compound B-1

Put 2-dibenzothiopheneboronic acid 3.3g, 1-bromo-3-odobenzene 4.0g, tetrakistriphenylphosphinepalladium (0) 0.31g, 2M aqueous sodium carbonate solution 25ml, dimethoxyethane 70ml into the flask and put in argon atmosphere Under reflux for 9 hours. After confirming the completion of the reaction by TLC, dichloromethane was added, washed with water and saturated brine, the organic layer was separated, the organic layer was dried over magnesium sulfate, filtered and concentrated to give a yellow oily substance . After purification by column chromatography, 3.96 g of white solid (Yield 83%, Intermediate B ) The results of FD-MS measurements on this product are shown below.

FD-MS: calcd C H BrS 339.25, found 339

 18 11

 Intermediate B3. 96 g was placed in a flask, and 40 ml of dehydrated tetrahydrofuran was dissolved under stirring in argon and stirred, then cooled to 70 ° C in a MeOH-dry ice bath, and 1.6 M normal butyllithium hexane was added thereto. 8 ml of the solution was added dropwise with a syringe. After stirring for 15 minutes, a solution of 1.35 ml of dichlorodiphenylsilane dissolved in 10 ml of dehydrated tetrahydrofuran was added dropwise. After the temperature was raised to 5 ° C, the completion of the reaction was confirmed by TLC, and the reaction was completed by adding a saturated aqueous solution of ammonium chloride. Dichloromethane was added, washed with water and saturated brine, the organic layer was separated, the solution was dried over magnesium sulfate, filtered and concentrated to give a colorless oily substance. A white solid was obtained after purification by column chromatography. This was washed 3 times with hexane and dried to obtain 2.49 g of Compound B-1 (68% yield). The results of FD-MS measurements on this product are shown below.

FD— MS: calcd C H S Si 700.98, found 700

 48 32 2

The resulting I匕合product B- 1 was used in the deposition 310 ° C, purified by sublimation in 5. 0 X 10- ⁶ Torr. The H PLC purity was 99.3%.

Synthesis Example 3 Synthesis of Compound B-2

 Intermediate c

4-dibenzothiopheneboronic acid 3.3 g, 1-bromo-3-iodobenzene 4.0 g, tetrakistriphenylphosphine palladium (0) 0.31 g, 2M aqueous sodium carbonate solution 25 ml, dimethoxyethane 70 ml were placed in a flask and argon atmosphere Under reflux for 9 hours. After confirming the completion of the reaction by TLC, add dichloromethane, wash with water and saturated brine, The organic layer was dried over magnesium sulfate, filtered and concentrated to give a yellow oily substance. After purification by column chromatography, 4.2 g of a white solid (yield 88%, intermediate C) was obtained. The results of FD-MS measurements on this product are shown below.

FD-MS: calcd C H BrS 339.25, found 339

 18 11

 Intermediate C4. Put Og in a flask, add 40 ml of dehydrated tetrahydrofuran under argon atmosphere, dissolve with stirring, cool to 70 ° C in MeOH dry ice bath, and to there 1.6 M normal butyl lithium hexane 8 ml of the solution was added dropwise with a syringe. After stirring for 15 minutes, a solution of 1.4 ml of dichlorodiphenylsilane dissolved in 10 ml of dehydrated tetrahydrofuran was added dropwise. After the temperature was raised to 5 ° C, the completion of the reaction was confirmed by TLC, and the reaction was terminated by caloring a saturated salt aqueous solution. Dichloromethane was added, washed with water and saturated brine, the organic layer was separated, the solution was dried over magnesium sulfate, filtered and concentrated to give a colorless oily substance. A white solid was obtained after purification by column chromatography. This was washed 3 times with hexane and dried to obtain 2.52 g of Compound B-2 (69% yield). The results of FD-MS measurements on this product are shown below.

FD— MS: calcd C H S Si 700.98, found 700

 48 32 2

The resulting I匕合product B- 2 was used in the deposition 310 ° C, purified by sublimation at 5. 5 X 10- ⁶ Torr. The H PLC purity was 99.3%.

Synthesis Example 4: Synthesis of C 2

 Compound C-2 was synthesized by the following synthesis route.

 [Chemical 29]

Intermediate A Intermediate A2. 48 g was placed in a flask, dissolved under stirring in 30 ml of dehydrated tetrahydrofuran under an argon atmosphere, cooled to 60 ° C in a MeOH dry ice bath, and then 1 5 ml of 6M normal butyl lithium hexane solution was added dropwise with a syringe. After stirring for 15 minutes, a solution of 1.30 g of diphenyl dichroic mouth germane dissolved in 13 ml of dehydrated tetrahydrofuran was added dropwise. After the temperature was raised to 5 ° C, the completion of the reaction was confirmed by TLC, and the reaction was completed by adding a saturated aqueous solution of ammonium chloride. Dichloromethane was added, washed with water and saturated brine, the organic layer was separated, the solution was dried over magnesium sulfate, filtered and concentrated to give a colorless oily substance. A white solid was obtained after purification by column chromatography. This was washed again with hexane and dried to obtain Compound C 2 1.6 lg (yield 67%). The results of FD-MS measurements on this product are shown below.

FD— MS: calcd C H 0 Ge 713.41, found 713

 48 32 2

The resulting I匕合product C-2 is 340 ° C, was used for deposition was purified by sublimation 1. 9 X 10- ³ Torr. The HPLC purity was 99.7%.

Synthesis Example 5: Synthesis of Compound C7

 Compound C-7 was synthesized by the following synthesis route.

[Chemical 30]

 Intermediate D

3, 5 Dibromobiphenyl 3. Place 08 g in a flask, dissolve 40 ml of dehydrated diethyl ether in an argon atmosphere with stirring, and cool to 60 ° C in a MeOH-dry ice bath. Normal butyllithium hexane solution 6.2 ml was dropped with a syringe. After raising the temperature to −10 ° C., the solution was cooled to 40 ° C., and a solution prepared by dissolving 1.36 g of diphenyl dichlore germane in 10 ml of dehydrated ethyl ether was added dropwise. -After raising the temperature to 10 ° C, the completion of the reaction was confirmed by TLC, and a saturated aqueous solution of ammonium chloride was added to terminate the reaction. Add dichloromethane, wash with water, separate the organic layer and dry the solution with magnesium sulfate. Thereafter, the mixture was filtered and concentrated to obtain a yellow oily substance. A white solid was obtained after purification by column chromatography. This was washed again with hexane and dried to obtain 2.85 g of Intermediate D (90% yield). The results of FD-MS measurements on this product are shown below.

 FD-MS: calcd C H Br Ge 691.01, found 691

 36 26 2

 Intermediate D total amount 2.85 g, 4 dibenzofuranboronic acid 1.85 g, tetrakis triphenyl phosphine palladium (0) 0.19 g, 2M aqueous sodium carbonate solution 19 g, dimethoxyethane 50 ml were put in a flask, under an argon atmosphere, Heated to reflux for 9 hours. After confirming the completion of the reaction by TLC, dichloromethane was added, washed with water and saturated brine, the organic layer was separated, the organic layer was dried over magnesium sulfate, filtered and concentrated to obtain an orange oily substance. . After purification by column chromatography, compound C-7 (yield 80%) was obtained as 2.86 g of a white solid. The results of FD-MS measurements on this product are shown below.

 FD— MS: calcd C H GeO 865.60, found 865

 60 40 2

The resulting I匕合product C-7 is 360 ° C, was used for deposition was purified by sublimation 3. 7 X 10- ⁶ Torr. The HPLC purity was 99.1%.

[0093] Synthesis Example 6: Synthesis of Compound D-2

 Compound D-2 was synthesized by the following synthesis route.

 [Chemical 31]

[0094] Intermediate C2. 57 g was placed in a flask, and 30 ml of dehydrated tetrahydrofuran was dissolved in an argon atmosphere while stirring and cooled to 70 ° C in a MeOH dry ice bath, to which 1.6 M normal butyllithium was added. 5 ml of hexane solution was added dropwise with a syringe. After stirring for 15 minutes, a solution of dichlorodiphenylgermane 1.Og dissolved in 15 ml of dehydrated tetrahydrofuran was added dropwise. After the temperature was raised to 12 ° C, the completion of the reaction was confirmed by TLC, and a saturated salt ammonium water solution was added to complete the reaction. Add dichloromethane, wash with water, separate the organic layer, The solution was dried over magnesium acid, filtered and concentrated to give a pale yellow oily substance. After purification by column chromatography, a white solid was obtained. This was washed twice with hexane and dried to obtain 1.97 g of Compound D-2 (yield 79%). The results of FD-MS measurements on this product are shown below.

 FD-MS: calcd C H S Ge 745.54, found 745

 48 32 2

The resulting I匕合product D-2 is 320 ° C, was used for deposition was purified by sublimation 7. 7 X 10- ⁶ Torr. The HPLC purity was 99.8%.

Synthesis Example 7: Synthesis of Compound A-7

 Compound A-7 was synthesized by the following synthesis route.

[Chemical 32]

 Intermediate E

3, 5—Dibromobiphenyl 3. Put Og in a flask, dissolve 40 ml of dehydrated diethyl ether in an argon atmosphere with stirring, and cool to 70 ° C in a MeOH dry ice bath. 6M normal butyl lithium hexane solution 6. Oml was added dropwise with a syringe. After the temperature was raised to 10 ° C, the solution was cooled to 40 ° C and a solution prepared by dissolving 0.92 g of diphenyldichlorosilane in 10 ml of dehydrated jetyl ether was added dropwise. After the temperature was raised to 0 ° C., the completion of the reaction was confirmed by TLC, and the reaction was completed by adding a saturated salt ammonium water solution. Dichloromethane was added, washed with water, the organic layer was separated, the solution was dried over magnesium sulfate, filtered and concentrated to give a yellow oily substance. A white solid was obtained after purification by column chromatography. This was washed again with hexane and dried to obtain 1.64 g of intermediate E (yield 58%). The results of FD-MS measurements on this product are shown below.

FD— MS: calcd CH Br Si 646.46, found 646 Intermediate E total amount 1.64 g, 4 dibenzofuranboronic acid 1.07 g, tetrakis triphenyl phosphine palladium (0) 0.12 g, 2M aqueous sodium carbonate solution 10 g, dimethoxyethane 40 ml were put in a flask, under an argon atmosphere, Heated to reflux for 8 hours. After confirming the completion of the reaction by TLC, dichloromethane was added, washed with water and saturated brine, the organic layer was separated, the organic layer was dried over magnesium sulfate, filtered and concentrated to obtain a yellow oily substance. . After purification by column chromatography, 1.87 g of white solid A-7 (90% yield) was obtained. The results of FD-MS measurements on this product are shown below.

 FD— MS: calcd C H SiO 821.04, found 821

 60 40 2

Compound A- 7 was used in the deposition 350 ° C, purified by sublimation at 6. IX 10- ⁶ Torr. The HPLC purity was 99.3%.

 [0097] The apparatus and measurement conditions used for FD-MS measurement in Synthesis Examples 1 to 7 are shown below.

 <FD—MS measurement>

 Device: HX110 (manufactured by JEOL Ltd.)

 Condition: Acceleration voltage 8kV

 Scan range m / z = 50-1500

 Emitter type: Carbon

 Emitter current: 0mA → 2mAZ min → 40mA (10 min hold)

[0098] Example 1 (Production of organic EL device)

A glass substrate having a thickness of 25 mm × 75 mm × 1.1 mm and having an ITO transparent electrode (Zomatic) was ultrasonically cleaned in isopropyl alcohol for 5 minutes, followed by UV ozone cleaning for 30 minutes. The glass substrate with the transparent electrode line after the cleaning is mounted on the substrate holder of the vacuum deposition apparatus. First, on the surface where the transparent electrode line is formed, the transparent electrode is covered to cover the transparent electrode with a thickness of Material ΗΤΜ was deposited. This HTM film functions as a hole injecting and transporting layer. Further, the compound A-2 obtained in Synthesis Example 1 as a host material and the complex K-1 were co-deposited by resistance heating on the hole injecting and transporting layer with a film thickness of 30 nm. The concentration of complex K 1 was 7% by weight. This film functions as a light emitting layer. Continuing on this light-emitting layer, the following material ETM1 has a film thickness of 25 nm. ETM2 was deposited 5 nm thick. The ETM1 layer and ETM2 layer function as an electron transport layer and an electron injection layer, respectively. Thereafter, LiF was used as an electron injecting electrode (cathode), and a film thickness of 1 nm was formed at a film formation rate of 1 A Zmin. Metal A1 was vapor-deposited on this LiF layer, and a metal cathode was formed to a thickness of 15 Onm to produce an organic EL device.

 (Emission performance evaluation of organic EL elements)

The organic EL device fabricated as described above was made to emit light by direct current drive, and an energization test was conducted. V, emission wavelength (λ), luminance (L), current density ω were measured, and current efficiency (LZJ) was obtained. . The results are shown in Table 1. In addition, with respect to the lifetime, the time when the initial luminance of 1500 cd / m ² is halved is measured, and the relative value with Comparative Example 1 as 100 is shown in Table 1.

[0099] [Chemical 33]

 E T M E T M 2

[0100] Examples 2 to 7

In Example 1, an organic EL device was prepared in the same manner except that the host material obtained in Synthesis Examples 2 to 7 described in Table 1 was used as the host material instead of Compound A-2. It was. About each obtained organic EL element, it carried out similarly to Example 1, and conducted the energization test and the lifetime measurement. The results are shown in Table 1.

 [0101] Comparative example:! ~ 4

 In Example 1, instead of Compound A-2 as a host material, International Publication WO2004

 <

 Z095598, JP-A-2005-310672, JP-A-2005-306864, and JP-A-2005-317275, respectively! An organic EL device was fabricated. About each obtained organic EL element, it carried out similarly to Example 1, and conducted the energization test and the lifetime measurement. Table 1 shows the results.

 [0102] [Chemical 34]

 Comparative compound 3 Comparative compound 4

[0103] [Table 1] Table 1

Example Host material Luminance (cd / nrf) Voltage (V) Emission wavelength (nm) Φ. . Example 1 A- 2 112 6.4 28 483 261 Example 2 B- 1 100 6.0 32 484 268 Example 3 102 5.8 29 483 327 Example 4 C- 2 108 6.0 35 484 251 Example 5 C-7 1 10 6.4 38 483 330 Example 6 D-2 102 6.2 35 484 292 Example 7 1 10 6.4 32 484 284 Comparative Example 1 Comparative Compound 1 98 7.0 20 484 100 Comparative Example 2 Comparative Compound 2 102 6.4 24 484 147 Comparative Example 3 Comparative Compound 3 104 6.9 22 484 94 Comparative Example 4 Comparative Compound 4 100 7.0 21 484 67 As shown in Table 1, all the host materials used in the comparative examples showed lower values of current efficiency than the host materials used in the examples, and both the voltage and the life were short.

Industrial applicability

 As described in detail above, when the organic EL element material having the compound power represented by the general formula (1) or (2) of the present invention is used, it has excellent luminous resistance with high luminous efficiency and pixel defects. And a long-life organic EL device.

 For this reason, the organic EL device of the present invention is extremely useful as a light source for various electronic devices.

Claims

Claims Materials for organic electoluminescence devices composed of compounds represented by the general formula (1) [Chemical formula 1]

[In General Formula (1), R to R are each independently a hydrogen atom, a halogen atom, or a substituent.

 1 8

May have a group, may have an alkyl group having 1 to 40 carbon atoms, may have a substituent, may have a heterocyclic group having 3 to 20 carbon atoms, and may have a substituent, may have 1 to 40 carbon atoms. It may have an alkoxy group or a substituent, may have a C6-C40 non-condensed aryl group, may have a substituent, may have a C6-C12 condensed aryl group, or a substituent. Good C6-C20 aryloxy group, may have a substituent, C7-C20 aralkyl group, may have a substituent, C2-C40 alkenyl group, substituent May have 1 to 40 alkylamino groups, may have substituents 7 to 60 carbon atoms aralkylamino groups, may have substituents 3 to 20 carbon atoms alkylsilyl groups, substituted An aryl group having 8 to 40 carbon atoms which may have a group, an aralkylsilyl group having 8 to 40 carbon atoms which may have a substituent, and a carbon number having 3 to 20 carbon atoms which may have a substituent Alkyl germanium group, may have a substituent, may have 8 to 40 carbon atoms aryl germanium group, may have a substituent, 8 to 40 carbon atoms aralkyl germanium group, have substituents It may be a 7 to 40 carbon atom group which may be substituted, a halogenated alkyl group having 1 to 40 carbon atoms which may have a substituent, a cyan group or a structure represented by the following general formula (a): R ~ R

 1 8 Among them, at least one has a structure represented by the following general formula (a).

[Chemical 2]

(In the general formula (a), L is a C1-C10 alkylene group which may have a single bond or a substituent, or a C6-C40 non-condensed arylene group which may have a substituent. , May have a substituent, may be a condensed arylene group having 6 to 12 carbon atoms, may have a substituent, and is a divalent aromatic heterocyclic group having 3 to 40 carbon atoms, Y to Y are Each independently may have a substituent

 13

A prime alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms which may have a substituent, and an aromatic heterocyclic group having 6 to 30 carbon atoms which may have a substituent. It is an elementary atom or a germanium atom. )

 X is a sulfur atom, an oxygen atom, a substituted silicon atom represented by SIR R or a substituted germanium atom represented by GeR R and abcd, and R 1, R 2, R and R each independently have a substituent abcd α

Or an alkyl group having 1 to 40 carbon atoms or an aryl group having 6 to 20 carbon atoms which may have a substituent. ]

 Material for organic electoluminescence device comprising a compound represented by the following general formula (2)

[In the general formula (2), R 1 to R 4 and R 5 independently represent a hydrogen atom, a halogen atom,

 11 14

An alkyl group having 1 to 40 carbon atoms that may have a substituent, a heterocyclic group having 3 to 20 carbon atoms that may have a substituent, and 1 to 40 carbon atoms that may have a substituent Or a non-condensed aryl group having 6 to 40 carbon atoms, or a substituent. A condensed aryl group of up to 12 carbon atoms, an optionally substituted aryl group having 6 to 20 carbon atoms, an optionally substituted carbon atom number of 7 to 20 aralkyl groups, and an optionally substituted carbon atom 2 to 40 alkyl groups, optionally having 1 to 40 alkylamino groups, and optionally having substituents, having 7 to 60 carbon atoms, having a substituent. Or an alkylsilyl group having 3 to 20 carbon atoms, an arylsilylsilyl group having 8 to 40 carbon atoms which may have a substituent, or a substituent, an aralkylsilyl group having 8 to 40 carbon atoms, or a substituent. May have a group, an alkyl germanium group having 3 to 20 carbon atoms, an aryl germanium group having 8 to 40 carbon atoms which may have a substituent, or a substituent! Aralkylgermanium group of ˜40, optionally substituted ketoaryl group having 7 to 40 carbon atoms, and optionally substituted carbon It is a halogenated alkyl group or cyan group having a prime number of 1 to 40.

 X is a sulfur atom, an oxygen atom, a substituted silicon atom represented by SIR R, or GeR R.

 a b c d is a substituted germanium atom, and R 1, R 2, R and R each independently have a substituent.

 a b c d

Or an alkyl group having 1 to 40 carbon atoms or an aryl group having 6 to 20 carbon atoms which may have a substituent.

 L may have a single bond or a substituent, an alkylene group having 1 to 10 carbon atoms, a substituent, a non-condensed arylene group having 6 to 40 carbon atoms, or a substituent. It may be a condensed arylene group having 6 to 12 carbon atoms or a substituent, and is a divalent aromatic heterocyclic group having 3 to 40 carbon atoms.

 Y represents an alkyl group having 1 to 10 carbon atoms which may have a substituent, an aryl group having 6 to 20 carbon atoms which may have a substituent, and 6 to 30 carbon atoms which may have a substituent. And when Y is plural, they may be the same or different.

 Z is a key atom or a germanium atom.

 n is an integer of 1 to 4. ]

 The compound power represented by following General formula (3) or (4) The organic electoluminescence material for luminescence elements of Claim 2.

[Chemical 4]

 (3) (4)

[In the general formulas (3) and (4), R to R are the same as R to R and R, and L, X, Z,

 11 17 11 14

 Y and n are the same as described above. ]

[4] At least one layer of the organic thin film layer is claimed in the case of an organic electoluminescence device in which one or more organic thin film layers each having at least a light emitting layer are sandwiched between the cathode and the anode. An organic electoluminescence device containing the material for an organic electoluminescence device according to any one of 1 to 3.

[5] The organic electoluminescence device according to [4], wherein the light emitting layer contains the organic electroluminescence device material as a host material.

6. The organic electroluminescent device according to claim 4, wherein the luminescent layer contains a host material and a phosphorescent luminescent material, and the host material is the material for the organic electroluminescent device.

 [7] The light-emitting layer contains a host material and a phosphorescent light-emitting material, and the phosphorescent light-emitting material is a compound containing iridium (Ir), osmium (Os), or platinum (Pt) metal. Item 5. The organic electoluminescence device according to item 4.

8. The organic electroluminescent element according to claim 4, wherein the light emitting layer contains a host material and a phosphorescent light emitting material, and the phosphorescent light emitting material is a light emitting material having a metal carbene carbon bond.

 [9] The organic electoluminescence device according to [4], wherein the light emitting layer includes a blue metal complex having a wavelength of maximum light emission luminance of 500 nm or less.

10. The organic electoluminescence device according to claim 4, further comprising an electron injection layer between the light emitting layer and the cathode, wherein the electron injection layer contains a nitrogen-containing ring derivative as a main component.

[11] The organic electoluminescence device has a hole transport layer, and the hole transport layer includes the hole transport layer. 5. The organic electroluminescence element according to claim 4, comprising a material for an organic electoluminescence element.

 [12] The organic electroluminescent mouth luminescence device has an electron transporting layer and a Z or hole blocking layer, and the electron transporting layer and Z or the hole blocking layer contain the organic electroluminescent port luminescence device material. 4. Organic electroluminescent device according to 4.

13. The organic electroluminescent device according to claim 4, wherein a reducing dopant is added to the interface region between the cathode and the organic thin film layer.